US10994048B2 - Method for manufacturing hyaluronate fibers by using melt spinning and hyaluronate fibers manufactured thereby - Google Patents

Method for manufacturing hyaluronate fibers by using melt spinning and hyaluronate fibers manufactured thereby Download PDF

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US10994048B2
US10994048B2 US15/757,605 US201615757605A US10994048B2 US 10994048 B2 US10994048 B2 US 10994048B2 US 201615757605 A US201615757605 A US 201615757605A US 10994048 B2 US10994048 B2 US 10994048B2
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hyaluronate
fiber
hyaluronate fiber
aqueous solution
spinning
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Dong Keon KWEON
Seung Hyeon PARK
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JINWOO BIO Co Ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/20—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
    • A61B17/00—Surgical instruments, devices or methods, e.g. tourniquets
    • A61B17/04—Surgical instruments, devices or methods, e.g. tourniquets for suturing wounds; Holders or packages for needles or suture materials
    • A61B17/06—Needles ; Sutures; Needle-suture combinations; Holders or packages for needles or suture materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
    • A61K31/728—Hyaluronic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
    • A61L17/06—At least partially resorbable materials
    • A61L17/10—At least partially resorbable materials containing macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/58—Materials at least partially resorbable by the body
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
    • A61L31/042—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00—Formation of filaments, threads, or the like
    • D01D5/08—Melt spinning methods
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F9/00—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/06—Flowable or injectable implant compositions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
    • C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2509/00—Medical; Hygiene
    • D10B2509/04—Sutures

Definitions

  • the present invention relates to a hyaluronate fiber, and more particularly to a hyaluronate fiber, suitable for use in a surgical suture, a filler for cosmetic surgery, a lifting thread, a tissue-engineering scaffold, etc., and a method of manufacturing the same.
  • Hyaluronic acid is a colorless high-viscosity polysaccharide having a molecular weight of 500,000 to 13,000,000 Da, and is configured such that D-glucuronic acid and N-acetylglucosamine, which are repeating units, are alternately linked by (1-3) and (1-4) bonds.
  • HA is involved in a variety of human physiological activities and is known to have various physiological activities depending on the molecular weight thereof.
  • polymeric HA is used as a space filler, and is known to possess anti-angiogenic and immunosuppressive functions.
  • HA of 2.0 MDa or more in the form of a high-viscosity hydrogel is currently widely utilized as an injecting agent for joints, a filler for cosmetic surgery, and an adhesion inhibitor for internal and external surgery.
  • most products are in the form of a liquid such as a high-viscosity aqueous solution or hydrogel, and are thus limited in usability, storability and processability.
  • the stability of HA itself decreases, and care should be taken to store and distribute the product.
  • the HA content in the actual product is as low as about 1 ⁇ 5%, making it impossible to inject high-concentration HA in a large amount into a human patient, and also, injection pressure due to the high volume thereof leads to great pain for the patient.
  • HA when HA is injected in vivo in the form of liquid, it is rapidly degraded by various lyases present in vivo to thus decrease the molecular weight thereof, whereby the persistence in vivo is also lowered and the effect on the treatment site is deteriorated.
  • Korean Patent Application Publication No. 2014-0100469 and Japanese Patent Application Publication No. 2011-31034 disclose a suture in which a safe degradable polymer as a main material is blended or coated with a small amount, specifically 10% or less, of HA, but are problematic because of low HA content.
  • the HA content may be increased upon production of a fiber composed exclusively of HA
  • a method of manufacturing a fiber composed exclusively of HA has not yet been known because it is impossible to melt HA owing to strong hydrogen bonding in the HA polymer polysaccharide.
  • the present inventors have made efforts to solve the above problems and thus have ascertained that, when non-melting hyaluronate is controlled in the water content thereof through pretreatment and is then melt spun, a sodium hyaluronate fiber, suitable for use in a surgical suture, a filler for cosmetic surgery, a tissue-engineering scaffold, and the like, may be manufactured, thus culminating in the present invention.
  • the present invention is intended to provide a hyaluronate fiber and a method of manufacturing the same, in which the hyaluronate fiber is composed mainly of a hyaluronate having excellent biocompatibility, skin elasticity and moisture retention.
  • the present invention is intended to provide a surgical suture, a filler for cosmetic surgery, a lifting thread, and a tissue-engineering scaffold, manufactured using the hyaluronate fiber having high safety and biocompatibility.
  • the present invention provides a method of manufacturing a hyaluronate fiber through melt spinning, comprising the steps of: (a) controlling the water content of a hyaluronate having a weight average molecular weight of 500 ⁇ 3,000 kDa to 5 ⁇ 20%; (b) producing a hyaluronate fiber by placing the hyaluronate having a controlled water content in a melt-spinning apparatus and performing heating to 150 ⁇ 200° C. and then high-pressure spinning; and (c) hardening the surface of the hyaluronate fiber by immersing the hyaluronate fiber in an ethanol aqueous solution.
  • the hyaluronate has a pH of 6 ⁇ 8.
  • the step of hardening the surface of the hyaluronate fiber comprises immersion once in the ethanol aqueous solution or immersion two to five times while sequentially increasing the ethanol concentration of the ethanol aqueous solution.
  • the ethanol aqueous solution has a concentration of 30 ⁇ 99 vol %.
  • the present invention provides a hyaluronate fiber, manufactured by the above method.
  • the present invention provides a surgical suture, a filler for cosmetic surgery, a lifting thread, and a tissue-engineering scaffold comprising the above hyaluronate fiber.
  • a hyaluronate fiber is manufactured using a hyaluronate as a main component and is thus excellent in safety and biocompatibility, and moreover, causes no microbial contamination, unlike typical liquid hydrogel products, and is easy to handle and use and can thus be utilized as formulations in various forms for tissue restoration.
  • the hyaluronate fiber of the present invention is a product in solid form, and thus the volume thereof relative to the hyaluronate concentration is very low to thus minimize the pain and discomfort of a patient upon in-vivo injection, thereby maximizing the therapeutic effect.
  • FIG. 1 shows a melt-spinning apparatus used in the present invention
  • FIG. 2 shows the DSC results before control of the water content of polymeric hyaluronate and after control of the water content thereof to 10%.
  • the present inventors have ascertained that, when hyaluronate, which is not melted due to strong hydrogen bonding, is subjected to wet treatment, melt spinning thereof becomes possible and a hyaluronate fiber having high hyaluronate content may be manufactured, and the properties of the hyaluronate fiber may be adjusted through surface hardening, thus culminating in the present invention.
  • an endothermic peak due to the melting of sodium hyaluronate having controlled water content is confirmed through measurement using a differential scanning calorimeter (DSC). Based on the measurement results, water content of sodium hyaluronate is controlled to 5 ⁇ 20%, and then melt spinning is performed at 150 ⁇ 200° C., thus manufacturing a sodium hyaluronate fiber. In order to improve the properties thereof, the sodium hyaluronate fiber is sequentially immersed in each of 50%, 70% and 95% ethanol aqueous solutions to thus harden the surface thereof, thereby yielding a hyaluronate fiber.
  • DSC differential scanning calorimeter
  • the manufactured sodium hyaluronate fiber can be found to maintain the properties and shape thereof even when immersed in saline for a long period of time.
  • an aspect of the present invention addresses a method of manufacturing a hyaluronate fiber through melt spinning, comprising the steps of: (a) controlling the water content of a hyaluronate having a weight average molecular weight of 500 ⁇ 3,000 kDa to 5 ⁇ 20%; (b) producing a hyaluronate fiber by placing the hyaluronate having a controlled water content in a melt-spinning apparatus and performing heating to 150 ⁇ 200° C. and then high-pressure spinning; and (c) hardening the surface of the hyaluronate fiber by immersing the hyaluronate fiber in an ethanol aqueous solution.
  • the hyaluronate is configured such that HA is coupled with a salt, and examples thereof may include, but are not limited to, sodium hyaluronate, calcium hyaluronate, potassium hyaluronate, etc.
  • any process may be performed without limitation, so long as the water content of the hyaluronate may be controlled.
  • the water content of the hyaluronate may be controlled using a thermo hygrostat.
  • the water content of the hyaluronate is less than 5%, it is difficult to perform a spinning process due to a difficulty in melting upon melt spinning under conditions of high temperature and high pressure. On the other hand, if the water content of the hyaluronate exceeds 20%, it is difficult to maintain the shape of the fiber even after the hardening process due to the high water content of the fiber after the spinning process.
  • the hyaluronate having a controlled water content of 5 ⁇ 20% is placed in the melt reservoir of a melt-spinning apparatus ( FIG. 1 ), heated to 150 ⁇ 200° C., and spun under high pressure, thus manufacturing a hyaluronate fiber.
  • hyaluronate fiber according to the present invention may be manufactured using hyaluronate alone, carrier or excipient components, which are typically used in the art, may be further added depending on the field of use thereof, and the kinds and amounts thereof are not particularly limited.
  • HA may be mixed with a cellulose material, which is a pharmacologically acceptable biocompatible agent, and with a highly degradable polymer, such as polyethylene, polydioxanone, polyvinyl alcohol, polyvinyl ether, polyvinyl pyrrolidone, or polylactic acid, and then spun.
  • a cellulose material which is a pharmacologically acceptable biocompatible agent
  • a highly degradable polymer such as polyethylene, polydioxanone, polyvinyl alcohol, polyvinyl ether, polyvinyl pyrrolidone, or polylactic acid
  • the hyaluronate fiber is immersed in an ethanol aqueous solution, and thus the surface thereof is hardened.
  • Hardening the surface of the sodium hyaluronate fiber is performed through immersion once (an immersion time of about 1 sec) in a 90 ⁇ 99 vol % ethanol aqueous solution or immersion two to five times (an immersion time of about 1 sec) while sequentially increasing the ethanol concentration of an ethanol aqueous solution.
  • the concentration of the ethanol aqueous solution that is used for surface hardening treatment is 30 ⁇ 99 vol %, and preferably 50 ⁇ 95 vol %.
  • a surface crosslinking step may be further conducted in a manner in which the surface-hardened sodium hyaluronate fiber is immersed in an aqueous solution of a crosslinking synthetic chemical, such as glutaraldehyde, epichlorohydrin, etc., or in an aqueous solution of a natural polymer material, which is cationic upon water dissolution, such as chitosan, polylysine, etc.
  • the sodium hyaluronate fiber, a portion of the surface of which is crosslinked may be improved in degradation resistance and mechanical properties.
  • Another aspect of the present invention addresses a hyaluronate fiber manufactured by the above method.
  • the hyaluronate fiber according to the present invention may be manufactured with a hyaluronate purity of 100%, and the surface thereof is firmly hardened or crosslinked, and thus the hyaluronate fiber of the invention has no microbial contamination, unlike existing liquid hyaluronate products for tissue restoration, and is easy to handle and use, and thus may be utilized as formulations in various forms for tissue restoration.
  • a further aspect of the present invention addresses a surgical suture, a filler for cosmetic surgery, a lifting thread, and a tissue-engineering scaffold comprising the aforementioned hyaluronate fiber.
  • Sodium hyaluronate (Hi-AquaTM, made by JinWOO Bio) having a molecular weight of 1.2 MDa was subjected to wet treatment using a thermo hygrostat. Specifically, 10 g of sodium hyaluronate was allowed to stand at a relative humidity of 60% for 1 ⁇ 3 hr, whereby the water content of the sodium hyaluronate was controlled to 5 ⁇ 30%. For reference, the water content of HA before wet treatment was about 2%.
  • the endothermic peaks of sodium hyaluronate before wet treatment and sodium hyaluronate subjected to wet treatment in Example 1 were measured under conditions of a temperature of 30 ⁇ 250° C. and a heating rate of 10° C./min using a differential scanning calorimeter (DSC6100, Seiko, Japan). Based on the results of DSC measurement, sodium hyaluronate powder not subjected to wet treatment was not detected in an endothermic peak due to melting, whereas sodium hyaluronate, the water content of which was controlled to 5% or more, was strongly detected in an endothermic peak due to melting in the temperature range of about 150 ⁇ 200° C. Accordingly, melt spinning of the sodium hyaluronate can be confirmed to be possible in the above temperature range.
  • Example 1 The sodium hyaluronate subjected to wet treatment in Example 1 was placed in the melt reservoir of a melt-spinning apparatus, spun at 150 ⁇ 200° C. under nitrogen pressure, and dried at room temperature in a typical manner, thus manufacturing a sodium hyaluronate fiber (HA fiber).
  • HA fiber sodium hyaluronate fiber
  • a HA fiber manufactured through spinning in the same manner as in Example 2, was sequentially immersed in 50% ethanol, 70% ethanol, and 95% ethanol to thus harden the surface thereof, followed by typical drying at room temperature, thereby manufacturing a sodium hyaluronate fiber (HA fiber).
  • a HA fiber manufactured through spinning in the same manner as in Example 2, was directly immersed in 95% ethanol to thus harden the surface thereof, followed by typical drying at room temperature, thereby manufacturing a sodium hyaluronate fiber (HA fiber).
  • Example 5 Production of HA Fiber Through Melt Spinning and Surface Hardening
  • a HA fiber manufactured through spinning in the same manner as in Example 2, was directly immersed in 50% ethanol to thus harden the surface thereof, followed by typical drying at room temperature, thereby manufacturing a sodium hyaluronate fiber (HA fiber).
  • the sodium hyaluronate fibers (HA fibers) of Examples 2 to 5 were immersed in saline at 37° C., and the swelling rate over time was measured. The results are shown in Table 1 below.
  • the swelling ratio was about 148%, from which the fiber surface was confirmed to be strongly hardened through hardening treatment to thus maintain the shape of the fiber.
  • the hyaluronate fiber of the present invention can be utilized for a surgical suture, a filler for cosmetic surgery, a tissue-engineering scaffold, etc.

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US15/757,605 2015-09-03 2016-09-01 Method for manufacturing hyaluronate fibers by using melt spinning and hyaluronate fibers manufactured thereby Active 2037-09-15 US10994048B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR1020150125088A KR101709608B1 (ko) 2015-09-03 2015-09-03 용융 방사에 의한 히알루론산염 파이버의 제조방법 및 이로부터 제조된 히알루론산염 파이버
KR10-2015-0125088 2015-09-03
PCT/KR2016/009748 WO2017039335A1 (fr) 2015-09-03 2016-09-01 Procédé de fabrication de fibres de hyaluronate à l'aide de filage par fusion, et fibres de hyaluronate fabriquées par ce dernier

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US20180243471A1 US20180243471A1 (en) 2018-08-30
US10994048B2 true US10994048B2 (en) 2021-05-04

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KR102426699B1 (ko) * 2020-11-26 2022-07-29 (주)진우바이오 히알루론산염 파이버 및 이의 제조방법
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CN108350610A (zh) 2018-07-31
EP3346032A4 (fr) 2019-04-10
EP3346032B1 (fr) 2020-01-01
US20180243471A1 (en) 2018-08-30
WO2017039335A1 (fr) 2017-03-09
JP6563141B2 (ja) 2019-08-21

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